CA2469764A1 - Use for the oleo-repellent paper sizing of carboxylic perfluoropolyethers - Google Patents
Use for the oleo-repellent paper sizing of carboxylic perfluoropolyethers Download PDFInfo
- Publication number
- CA2469764A1 CA2469764A1 CA002469764A CA2469764A CA2469764A1 CA 2469764 A1 CA2469764 A1 CA 2469764A1 CA 002469764 A CA002469764 A CA 002469764A CA 2469764 A CA2469764 A CA 2469764A CA 2469764 A1 CA2469764 A1 CA 2469764A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- molecular weight
- cf2cf
- cf2o
- integers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/16—Sizing or water-repelling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Polyethers (AREA)
Abstract
Use for the oleo-repellent paper sizing of carboxylic perfluoropolyethers of formula (I) T-O-R f-T
wherein T = -CF2-COOH or -CF2CF2-COOH and R f is a (per)fluoropolyoxyalkylene chain.
wherein T = -CF2-COOH or -CF2CF2-COOH and R f is a (per)fluoropolyoxyalkylene chain.
Claims (2)
1. Use for the oleo-repellent paper sizing of perfluoropol-yethers having the following structure:
(I) T-O-R f-T
wherein - T = -CF2-COOH or -CF2CF2-COOH;
- R f is a (per) fluoropolyoxyalkylene chain, having number average molecular weight in the range 500-10,000, formed of one or more repeating units, statistically distributed along the chain, having the following structure:
(CFXO) , (CF2CF2O) , (CF2CF2CF2O) , (CF2CF2CF2CF2O), (CR4R5CF2CF2O), (CF(CF3)CF2O), (CF2CF(CF3)O), wherein X = F, CF3; R4 and R5, equal to or different from each other, are selected among H, Cl, or per-fluoroalkyl from 1 to 4 carbon atoms.
(I) T-O-R f-T
wherein - T = -CF2-COOH or -CF2CF2-COOH;
- R f is a (per) fluoropolyoxyalkylene chain, having number average molecular weight in the range 500-10,000, formed of one or more repeating units, statistically distributed along the chain, having the following structure:
(CFXO) , (CF2CF2O) , (CF2CF2CF2O) , (CF2CF2CF2CF2O), (CR4R5CF2CF2O), (CF(CF3)CF2O), (CF2CF(CF3)O), wherein X = F, CF3; R4 and R5, equal to or different from each other, are selected among H, Cl, or per-fluoroalkyl from 1 to 4 carbon atoms.
2. Use according to claim 1, wherein R f is selected from:
(A) -(CF2CF(CF3)O)a(CFYO)b-wherein Y is F or CF3 ; a and b are integers such that the molecular weight is within the above range;
a/b is between 10 and 100;
or the repeating units indicated in (A) can be linked as follows:
- (CF2CF(CF3)O)a(CFYO)b-CF2(R' f)CF2-O-(CF2CF(CF3)O)a(CFYO)b-wherein R'f is a fluoroalkylene group from 1 to 4 C atoms;
- (CF2CF2O)C(CF2O)d(CF2(CF2)z O)h-wherein c; d and h are integers such that the mole-cular weight is within the above range, h can be equal to 0; c/d is between 0.1 and 10; h/(c+d) is between 0 and 0.05; z is 2 or 3;
- (CF2CF(CF3)O)e(CF2CF2O)f(CFYO)g-wherein Y is F or CF3; e, f, g are integers such that the molecular weight is within the above range;
e/(f+g) is between 0.1 and 10, f/g is between 2 and 10;
- (CF2(CF2)z O)s-wherein s is an integer such to give the above molecular weight, z has the already defined meaning;
-(CR4R5CF2CF2O)j, -wherein R4 and R5 are equal to or different from each other and selected from H, Cl or perfluoro-alkyl, for example having 1-4 C atoms, j' being an integer such that the molecular weight be that above indicated; said units inside the fluoropolyoxy-alkylene chain can be linked with each other as fol-lows:
-(CR4R5CF2CF2C)p, -R' f-O- (CR4R5CF2CF2O)q, -wherein R'f is a fluoroalkylene group, for example from 1 to 4 C atoms; p' and q' are integers such that the molecular weight be that above mentioned;
(F) -(CF(CF3)CF2O)j"-(R'f)-O-(CF(CF3)CF2O)j"
j" being an integer such as to give the above molecular weight, R'f is a fluoroalkylene group from 1 to 4 C atoms.
Use according to claim 2, wherein the perfluoropolyether has formula (IV) T" -O- (CF2CF2O)m(CF2O)n-T"
wherein T"= -CF2-COOH, T'= -CF2CF2-COOH and the m, n, in-dexes are integers, such that the number average molecu-lar weight is in the range 500-10,000, preferably 1,000-4,000 and the m/n ratio is between 0.1 and 10.
Use according to claims 1-3, wherein the compounds of formula (I) are used in the form of salts solubilized or emulsified in water or in mixtures of water with alcoho-1s; glycols, ethers, wherein the alcohols are selected from isopropanol, ethanol, methanol, t-butanol; the ether is the dipropylenglycol monomethylether; the glycols are selected between ethylene or propylene glycol.
Aqueous compositions comprising:
A) from 1 to 60% by weight, preferably from 15 to 25%
by weight of a compound of formula (I) in a salified form and optionally B) from 0.5 to 25% by weight, preferably from 1 to 5%
by weight of a solvent selected from alcohols, glycols, ethers, preferably selected. among iso-propanol, ethanol, methanol, t-butanol, dipropylenglycol monomethylether, ethylene glycol, propylene glycol;
C) water as complement to 100.
6. Compositions according to claim 5, wherein the salt ca-tions are selected from alkaline metals, ammonium, and primary, secondary or tertiary amines in protonated form.
7. Use for the oleo-repellent paper sizing of the aqueous compositions of claims 4-5.
8. Oleo-repellent paper obtainable by treatment with the compositions of claims 5-6, containing from 0.05 to 2% by weight with respects to the dry cellulose of an acid of formula (I) of claim 1 or one of its salts.
(A) -(CF2CF(CF3)O)a(CFYO)b-wherein Y is F or CF3 ; a and b are integers such that the molecular weight is within the above range;
a/b is between 10 and 100;
or the repeating units indicated in (A) can be linked as follows:
- (CF2CF(CF3)O)a(CFYO)b-CF2(R' f)CF2-O-(CF2CF(CF3)O)a(CFYO)b-wherein R'f is a fluoroalkylene group from 1 to 4 C atoms;
- (CF2CF2O)C(CF2O)d(CF2(CF2)z O)h-wherein c; d and h are integers such that the mole-cular weight is within the above range, h can be equal to 0; c/d is between 0.1 and 10; h/(c+d) is between 0 and 0.05; z is 2 or 3;
- (CF2CF(CF3)O)e(CF2CF2O)f(CFYO)g-wherein Y is F or CF3; e, f, g are integers such that the molecular weight is within the above range;
e/(f+g) is between 0.1 and 10, f/g is between 2 and 10;
- (CF2(CF2)z O)s-wherein s is an integer such to give the above molecular weight, z has the already defined meaning;
-(CR4R5CF2CF2O)j, -wherein R4 and R5 are equal to or different from each other and selected from H, Cl or perfluoro-alkyl, for example having 1-4 C atoms, j' being an integer such that the molecular weight be that above indicated; said units inside the fluoropolyoxy-alkylene chain can be linked with each other as fol-lows:
-(CR4R5CF2CF2C)p, -R' f-O- (CR4R5CF2CF2O)q, -wherein R'f is a fluoroalkylene group, for example from 1 to 4 C atoms; p' and q' are integers such that the molecular weight be that above mentioned;
(F) -(CF(CF3)CF2O)j"-(R'f)-O-(CF(CF3)CF2O)j"
j" being an integer such as to give the above molecular weight, R'f is a fluoroalkylene group from 1 to 4 C atoms.
Use according to claim 2, wherein the perfluoropolyether has formula (IV) T" -O- (CF2CF2O)m(CF2O)n-T"
wherein T"= -CF2-COOH, T'= -CF2CF2-COOH and the m, n, in-dexes are integers, such that the number average molecu-lar weight is in the range 500-10,000, preferably 1,000-4,000 and the m/n ratio is between 0.1 and 10.
Use according to claims 1-3, wherein the compounds of formula (I) are used in the form of salts solubilized or emulsified in water or in mixtures of water with alcoho-1s; glycols, ethers, wherein the alcohols are selected from isopropanol, ethanol, methanol, t-butanol; the ether is the dipropylenglycol monomethylether; the glycols are selected between ethylene or propylene glycol.
Aqueous compositions comprising:
A) from 1 to 60% by weight, preferably from 15 to 25%
by weight of a compound of formula (I) in a salified form and optionally B) from 0.5 to 25% by weight, preferably from 1 to 5%
by weight of a solvent selected from alcohols, glycols, ethers, preferably selected. among iso-propanol, ethanol, methanol, t-butanol, dipropylenglycol monomethylether, ethylene glycol, propylene glycol;
C) water as complement to 100.
6. Compositions according to claim 5, wherein the salt ca-tions are selected from alkaline metals, ammonium, and primary, secondary or tertiary amines in protonated form.
7. Use for the oleo-repellent paper sizing of the aqueous compositions of claims 4-5.
8. Oleo-repellent paper obtainable by treatment with the compositions of claims 5-6, containing from 0.05 to 2% by weight with respects to the dry cellulose of an acid of formula (I) of claim 1 or one of its salts.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2003A001105 | 2003-06-03 | ||
| IT001105A ITMI20031105A1 (en) | 2003-06-03 | 2003-06-03 | USE FOR THE OIL REPELLENT TREATMENT OF CARBOSSYL PERFLUOROPOLYET PAPER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2469764A1 true CA2469764A1 (en) | 2004-12-03 |
| CA2469764C CA2469764C (en) | 2012-10-09 |
Family
ID=30131128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2469764A Expired - Fee Related CA2469764C (en) | 2003-06-03 | 2004-05-31 | Use for the oleo-repellent paper sizing of carboxylic perfluoropolyethers |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7534323B2 (en) |
| EP (1) | EP1484445B1 (en) |
| JP (1) | JP4892176B2 (en) |
| KR (1) | KR101128013B1 (en) |
| CN (1) | CN100404756C (en) |
| AU (1) | AU2004202453B2 (en) |
| BR (1) | BRPI0401883B1 (en) |
| CA (1) | CA2469764C (en) |
| DE (1) | DE602004007436T2 (en) |
| HK (1) | HK1073143A1 (en) |
| IT (1) | ITMI20031105A1 (en) |
| MX (1) | MXPA04005314A (en) |
| NZ (1) | NZ533059A (en) |
| TW (1) | TWI354006B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20031104A1 (en) * | 2003-06-03 | 2004-12-04 | Solvay Solexis Spa | CARBOXYLIC ACIDS (PER) FLUOROPOLYEREOUS AND THEIR USE FOR THE OIL REPELLENT TREATMENT OF PAPER |
| ITMI20050188A1 (en) | 2005-02-10 | 2006-08-11 | Solvay Solexis Spa | WATER COMPOSITIONS CONTAINING PERFLUOROPOLIETER DI-CARBOXYLIS SALTS FOR THE OLEOREPELLENT TREATMENT OF PAPER |
| EP1941099A1 (en) * | 2005-07-22 | 2008-07-09 | International Paper Company | Paper substrate containing a fluorine containing compound and having enhanced grease-resistance and glueability |
| US20070261807A1 (en) * | 2006-05-12 | 2007-11-15 | Taggart Thomas E | Use of polyvinylamine to improve oil and water sizing in cellulosic products |
| DE102007030102B4 (en) * | 2007-06-28 | 2019-10-31 | Schoeller Technocell Gmbh & Co. Kg | prepreg |
| KR101556810B1 (en) * | 2008-07-01 | 2015-10-01 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | Process for imparting grease, oil and water repellence to substrates |
| EP2576656A1 (en) | 2010-06-01 | 2013-04-10 | Solvay Specialty Polymers Italy S.p.A. | Fluoropolyether phosphate derivatives |
| US8647471B2 (en) * | 2010-12-22 | 2014-02-11 | Bayer Materialscience Llc | Process for the production of sized and/or wet-strength papers, paperboards and cardboards |
| FR2980491B1 (en) | 2011-09-27 | 2014-12-26 | Oberthur Technologies | PROCESS FOR SURFACE TREATMENT OF SECURITY DOCUMENT |
| US8771470B2 (en) | 2012-01-17 | 2014-07-08 | Agc Chemicals Americas, Inc. | Method of preparing a treated article and treated article formed therefrom |
| WO2015025929A1 (en) * | 2013-08-23 | 2015-02-26 | ダイキン工業株式会社 | Bifunctional compound containing perfluoro(poly)ether group, composition which contains bifunctional compound containing perfluoro(poly)ether group, and methods for producing said compound and said composition |
| WO2017102670A1 (en) | 2015-12-17 | 2017-06-22 | Solvay Specialty Polymers Italy S.P.A. | Composition of (per)fluoropolyethers for the treatment of cellulosic substrates |
| WO2019081258A1 (en) | 2017-10-25 | 2019-05-02 | Solvay Sa | Process for imparting grease, oil and water repellence to substrates |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492374A (en) * | 1963-06-14 | 1970-01-27 | Du Pont | Polyfluoropolyoxa-alkyl phosphates |
| US3665041A (en) | 1967-04-04 | 1972-05-23 | Montedison Spa | Perfluorinated polyethers and process for their preparation |
| JPS5112392A (en) * | 1974-07-22 | 1976-01-30 | Shinnitsuto Kagaku Kk | Futsusokeihatsusuihatsuyuzai |
| US4426466A (en) * | 1982-06-09 | 1984-01-17 | Minnesota Mining And Manufacturing Company | Paper treatment compositions containing fluorochemical carboxylic acid and epoxidic cationic resin |
| DE3486428T2 (en) | 1983-12-26 | 1996-10-10 | Daikin Ind Ltd | Halogen containing polyether |
| IT1201470B (en) * | 1985-09-24 | 1989-02-02 | Montefluos Spa | USE OF PERFLUOROPOLYETER DERIVATIVES FOR THE PROTECTION OF STONE MATERIALS FROM ATMOSPHERIC AGENTS |
| US4861836A (en) * | 1986-12-23 | 1989-08-29 | Daikin Industries Ltd. | Novel, iodine-containing compound, preparation thereof and block copolymer comprising the same |
| US5211861A (en) * | 1988-09-19 | 1993-05-18 | Ausimont S.R.L. | Liquid aqueous compositions comprising perfluoropolyethereal compounds suitable as lubricants in the plastic processing of metals |
| EP0462063A1 (en) * | 1990-06-13 | 1991-12-18 | Ciba-Geigy Ag | Fluorinated paper sizes |
| JPH04146917A (en) * | 1990-10-11 | 1992-05-20 | Asahi Chem Ind Co Ltd | Water/oil repellent |
| IT1269886B (en) * | 1994-06-14 | 1997-04-15 | Ausimont Spa | PROCESS FOR SURFACE TREATMENT OF CELLULOSE, METAL, GLASS, OR CEMENT, MARBLE, GRANITE AND SIMILAR MATERIALS |
| US5955556A (en) * | 1995-11-06 | 1999-09-21 | Alliedsignal Inc. | Method of manufacturing fluoropolymers |
| IT1290462B1 (en) * | 1997-04-08 | 1998-12-03 | Ausimont Spa | MODIFIED HYDROGENATED POLYMERS |
| IT1303808B1 (en) * | 1998-12-01 | 2001-02-23 | Ausimont Spa | SURFACE TREATMENTS WITH BIFUNCTIONAL DIPERFLUOROPOLYETER DERIVATIVES. |
| AU2001295603A1 (en) * | 2000-10-16 | 2002-04-29 | Chemguard Incorporated | Mono- and polyamides of perfluoroalkyl-substituted unsaturated acids |
| US6632508B1 (en) * | 2000-10-27 | 2003-10-14 | 3M Innovative Properties Company | Optical elements comprising a polyfluoropolyether surface treatment |
| US6638622B2 (en) * | 2001-01-11 | 2003-10-28 | Hitachi Global Storage Technologies | Perfluorinated polyethers with metal carboxylate end groups as anti-wetting and corrosion-protective agents |
| US6803109B2 (en) * | 2001-03-09 | 2004-10-12 | 3M Innovative Properties Company | Water-and oil-repellency imparting urethane oligomers comprising perfluoroalkyl moieties |
| US6737489B2 (en) * | 2001-05-21 | 2004-05-18 | 3M Innovative Properties Company | Polymers containing perfluorovinyl ethers and applications for such polymers |
| ITMI20011424A1 (en) * | 2001-07-05 | 2003-01-05 | Ausimont Spa | DISPERSIONS OF FLUORINATED POLYMERS |
| ITMI20020057A1 (en) | 2002-01-15 | 2003-07-15 | Ausimont Spa | AQUEOUS COMPOSITIONS OF PERFLUOROPOLYETHER PHOSPHATES AND THEIR USE TO CONFER THE PAPER WITH OIL REPELLENCE |
| ITMI20020056A1 (en) | 2002-01-15 | 2003-07-15 | Ausimont Spa | AQUEOUS COMPOSITIONS OF PERFLUOROPOLYETHER PHOSPHATES AND THEIR USE TO CONFER THE PAPER WITH OIL REPELLENCE |
| US6833418B2 (en) * | 2002-04-05 | 2004-12-21 | 3M Innovative Properties Company | Dispersions containing perfluorovinyl ether homopolymers and use thereof |
| ITMI20031104A1 (en) * | 2003-06-03 | 2004-12-04 | Solvay Solexis Spa | CARBOXYLIC ACIDS (PER) FLUOROPOLYEREOUS AND THEIR USE FOR THE OIL REPELLENT TREATMENT OF PAPER |
-
2003
- 2003-06-03 IT IT001105A patent/ITMI20031105A1/en unknown
-
2004
- 2004-05-20 NZ NZ533059A patent/NZ533059A/en not_active IP Right Cessation
- 2004-05-25 TW TW093114758A patent/TWI354006B/en not_active IP Right Cessation
- 2004-05-27 DE DE602004007436T patent/DE602004007436T2/en not_active Expired - Lifetime
- 2004-05-27 EP EP04012507A patent/EP1484445B1/en not_active Expired - Lifetime
- 2004-05-31 BR BRPI0401883-4A patent/BRPI0401883B1/en not_active IP Right Cessation
- 2004-05-31 CA CA2469764A patent/CA2469764C/en not_active Expired - Fee Related
- 2004-06-02 US US10/858,199 patent/US7534323B2/en not_active Expired - Fee Related
- 2004-06-02 JP JP2004164589A patent/JP4892176B2/en not_active Expired - Fee Related
- 2004-06-02 MX MXPA04005314A patent/MXPA04005314A/en active IP Right Grant
- 2004-06-03 AU AU2004202453A patent/AU2004202453B2/en not_active Ceased
- 2004-06-03 KR KR1020040040482A patent/KR101128013B1/en not_active IP Right Cessation
- 2004-06-03 CN CNB2004100714493A patent/CN100404756C/en not_active Expired - Fee Related
-
2005
- 2005-07-07 HK HK05105720.1A patent/HK1073143A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI354006B (en) | 2011-12-11 |
| US7534323B2 (en) | 2009-05-19 |
| KR20040104428A (en) | 2004-12-10 |
| BRPI0401883B1 (en) | 2014-12-16 |
| KR101128013B1 (en) | 2012-04-23 |
| ITMI20031105A0 (en) | 2003-06-03 |
| CA2469764C (en) | 2012-10-09 |
| AU2004202453B2 (en) | 2009-03-26 |
| EP1484445B1 (en) | 2007-07-11 |
| CN100404756C (en) | 2008-07-23 |
| ITMI20031105A1 (en) | 2004-12-04 |
| TW200506012A (en) | 2005-02-16 |
| HK1073143A1 (en) | 2005-09-23 |
| NZ533059A (en) | 2006-03-31 |
| CN1576459A (en) | 2005-02-09 |
| DE602004007436T2 (en) | 2008-04-30 |
| BRPI0401883A (en) | 2005-07-05 |
| JP2004360165A (en) | 2004-12-24 |
| DE602004007436D1 (en) | 2007-08-23 |
| JP4892176B2 (en) | 2012-03-07 |
| US20050000668A1 (en) | 2005-01-06 |
| MXPA04005314A (en) | 2004-12-07 |
| EP1484445A1 (en) | 2004-12-08 |
| AU2004202453A1 (en) | 2004-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180531 |